Hypofluorous acid, trifluoromethyl ester → HCID 4111754, compound

HRID 2058283Notes

Reaction equation

HRID 2058283 reaction equation
[CH3:1][N:2]([C:4]([O:12][Si](C)(C)C)=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:3].[F:17]OC(F)(F)F>ClC(F)(F)F>[F:17][CH:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:4]([N:2]([CH3:3])[CH3:1])=[O:12]

Participants

4

Reactant 2

HCID 78989Hypofluorous acid, trifluoromethyl esterHCID 54544702HCID 54544702, compound

Product 1

HCID 4111754HCID 4111754, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6392ChlorotrifluoromethaneSolvent

Procedure

A solution of 3.0 g (0.0127 mol) of β-(N,N-dimethylamino)-β-(trimethylsiloxy)styrene (from above) in 100 ml of chlorotrifluoromethane was cooled to -70° C. and 1.6 g (0.013 mol) of trifluoromethyl hypofluorite were passed into the solution over a period of 3 hours. The reaction mixture was warmed to room temperature and then distilled to give 1.49 g (65% yield) of α-fluoro-N,N-dimethylbenzeneacetamide as a colorless oil: bp 98°-100° C. (0.45 mm); 19F NMR (CCl3F) δ-175.9 ppm (d,J=50 Hz); 1H NMR (CCl3F) δ 2.86 ppm (s, 6H), 5.54 ppm (d,J=50 Hz, 1H) and 7.10-7.8 ppm (m, 5H). Anal. Calcd for C10H12FNO: C, 66.27; H, 6.68; F, 10.49; N, 7.73; Found: C, 66.41; H, 6.75; F, 10.30; N, 7.70.

Workup

  1. distillationdistilled

Sources & evidence

ORD record
ord-6d4221540e79495c8478b3f26e7bdeb8
Source dataset
uspto-grants-1980_07
Patent number
US04215044

Reaction notes

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